3,3-Dimethyl-6-nitro-1,3-dihydro-2H-indol-2-one → 6-Amino-3,3-dimethyl-1,3-dihydro-2H-indol-2-one

HRID 1507550Notes

Reaction equation

HRID 1507550 reaction equation
[CH3:1][C:2]1([CH3:15])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:14]>[Pd].C(OCC)(=O)C>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([CH3:15])([CH3:1])[C:3](=[O:14])[NH:4]2)=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 135892273,3-Dimethyl-6-nitro-1,3-dihydro-2H-indol-2-one

Product 1

HCID 135892296-Amino-3,3-dimethyl-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Palladium on activated carbon (10%, 129 mg, 121 μmol) was added to a solution of 3,3-dimethyl-6-nitroindolin-2-one (J.-P. Hölck et al., 1987, U.S. Pat. No. 4,666,923 A1; 500 mg, 2.42 mmol) in ethyl acetate (100 ml). The mixture was stirred at 70° C. under an hydrogen atmosphere (balloon) for 48 hours. The catalyst was filtered off, washed with ethyl acetate and the solvent was evaporated. The title compound was obtained as orange powder (427 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethyl acetate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9183d79a62bd4c96aafac326fc16e9a0
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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